The present invention is directed to the fermentation of a novel species of Streptomyces known as Streptomyces longwoodensis (X-14537) to produce the known polyether antibiotic lysocellin.
The polyether antibiotic lysocellin was first reported by Ebata et al. in J. Antibiotics, No. 2, Vol. 28, pp. 118-121 (1975).
The sodium salt of lysocellin forms colorless needles and melts at 158.degree. - 160.degree. C. The optical rotation is [.alpha.].sub.D.sup.25 + 11.5.degree. (c 1, methanol) and the compound exhibits an absorption maximum of low intensity at 292 nm (E.sub.1.sup.1%.sub.cm 0.68 in ethanol).
In infrared spectrum (KBr), characteristic bands were observed at 3450.about.3300 cm.sup.-.sup.1 corresponding to hydroxyl group; 2960 and 2930 cm.sup.-.sup.1 corresponding to methyl and methylene groups; 1710 and 1590 cm.sup.-.sup.1 corresponding to carbonyl groups. Elementary analysis and measurement of the molecular weight (656) by the vapor pressure equilibrium method indicated a molecular formula C.sub.34 . C.sub.34 H.sub.59 O.sub.10 Na.sup.. 1/2H.sub.2 O (molecular weight 659) for sodium salt of lysocellin.
Calcd. for C.sub.34 H.sub.59 O.sub.10 Na.sup.. 1/2 H.sub.2 O: C, 61.88; H, 9.18; O, 25.46; Na 3.48. Found: C, 61.58; H, 9.10; O, 25.05; Na, 3.37.
Lysocellin is a monocarboxylic acid with pKa' of 6.6 when titrated in 66% dimethylformamide. The sodium salt of lysocellin is soluble in methanol, ethanol, n-butanol, ethyl acetate, benzene and chloroform, and insoluble in water. Lysocellin is stable in neutral solution but labile in acidic solution.
It produces a positive reaction to 2,4-dinitrophenylhydrazine and turns brown with concentrated sulfuric acid. The compound gives negative reactions to potassium permanganate, ferric chloride and MOLISCH reactions. On thin-layer chromatograms of silica gel, the following Rf values were observed: 0.54 with ethyl acetate, 0.30 with benzene-methanol (9:1), 0.63 with chloroform-methanol (9:1).